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Vacation Rentals in Kailua, HI

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All 116 Rentals in Kailua
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Travelers to Kailua are booking February dates now. Secure your vacation rental today, and have the perfect trip.
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From
$126
Per Night
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1 / 16
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1 Bedroom, 1 Bathroom, Sleeps 2
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From
$290
Per Night
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1 / 10
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3 Bedrooms, 1 Bathroom, Sleeps 6
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$145
Per Night
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1 / 32
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1 Bedroom, 1 Bathroom, Sleeps 3
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From
$139
Per Night
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1 / 7
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Outdoor Dining Area
  • Air Conditioning
  • Microwave
  • TV
  • Linens Provided
  • Hairdryer
  • Internet Access
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Walk to Kailua Beach or Town. Located at: 131 Kuulei Road Kailua, Hawaii The Ginger Studio at the Hawaii Sheffield House has its own 'secret garden' is a delightful home away from home for your Hawaii vacation. The Secret Garden is shaded by a kukui tree and has its own outside dining table and... View all property information
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4 of 5 stars Reviewed January 31, 2014
We were surprised just how spacious this studio is and how nice and fresh it is. Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
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From
$174
Per Night
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1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Parking
  • Grill
  • Air Conditioning
  • Ceiling Fans
  • Hairdryer
  • Refrigerator
  • Outdoor Dining Area
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaii Sheffield House is located only 10 houses to Kailua Beach. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite has free off street parking, free wifi, cable TV, boogie boards and a first morning complementary continental breakfast. The... View all property information
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From
$1,050
Per Night
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1 / 31
6 Bedrooms, 5 Bathrooms, Sleeps 12
Details Reviews (4) Make Inquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Grill
  • Parking
  • TV
  • Waterfront
  • Linens Provided
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Seaside is a classic beachfront estate reminiscent of 'Old Hawaii'. Coconut trees abound throughout the spacious lush green lawns. WIth large open spaces, both inside and out, this home is perfect for big families or family reunions. Seaside sits on Kailua Beach, one of the most beautiful beaches... View all property information
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5 of 5 stars Reviewed August 16, 2014
The pictures do not provide justice to the true beauty and convenience of the yard and beach. It is spectacular! The house is large and comfortable . It worked well for my...
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From
$150
Per Night
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1 / 18
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Grill
  • Patio
  • Internet Access
  • VCR
  • Microwave
  • TV
  • Satellite TV
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
A private 400 sq foot studio w/fenced courtyard/lanai, in quiet Kaimalino. Relax outdoors or indoors w/full kitchen, bath, cable and internet connections. A short walk will take you to a turtle nesting grounds, the open ocean facing Maui and Lanai islands, sandy Kailua Beach, and Aikahi Shopping... View all property information
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4 of 5 stars Reviewed August 13, 2014
This studio was exactly as advertised and more. It was an easy walk to a beautiful sunrise, supermarkets and restaurants but out of the way enough to avoid the traffic and noise...
5 of 5 stars Reviewed January 8, 2014
This proved a really great choice , the condo is lovely and in a really quiet and peaceful area. Plenty of space and a nice garden with plenty of seating . The owner lives next...
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From
$95
Per Night
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1 / 11
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1 Bedroom, 1 Bathroom, Sleeps 4
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Details Reviews (3) Make Inquiry
Amenities & Details
  • TV
  • Washer
  • Parking
  • Internet Access
  • Satellite TV
  • Dryer
  • Grill
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This is a great 300 sq ft studio only 3 min drive to world famous kailua beach This studio has a cal king bed and a futon that can sleep 4 people 55 in flat screen TV free wi-fi kitchen with everything you need to cook all your meals natural stone shower that is very roomy and a tiled swimming... View all property information
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5 of 5 stars Reviewed September 28, 2014
John was an incredible host very resourceful and kind always there whenever my wife or I had a question told us all the good restaurants. Very happy great value, clean, bikes...
3 of 5 stars Reviewed July 6, 2014
Looking for a deal on our Hawaiian getaway, I booked this place after another fell through. I was trying to be thrifty and this looked like it fit our needs. The place is...
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From
$575
Per Night
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1 / 13
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Washer
  • Stereo System
  • Refrigerator
  • Grill
  • Stove
  • Microwave
  • Dryer
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Just one house off the beach this 4 bedroom 3 three bedroom home is perfect for the family holiday. It was completely renovated in December 2014. New walls, new floors (travertine stone and hardwood, carpet in the bedrooms new bathrooms. New cabinets, new granite counter tops. New appliances well... View all property information
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From
$499
Per Night
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1 / 16
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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Details Reviews (2) Make Inquiry
Amenities & Details
  • Dryer
  • Microwave
  • Patio
  • Parking
  • Ceiling Fans
  • Satellite TV
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Experience Hawaii at it's fullest by staying at this amazing 1926 bungalow located between two of the most beautiful beaches in the world. Lanikai and Kailua beaches are just 200 yards away. Kayak, Bicycle, Surfboard, Paddle board and Snorkel Rentals are 200 yards away at Kailua Beach Park. A... View all property information
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5 of 5 stars Reviewed July 18, 2014
We had two families totaling 4 adults and 5 kids stay at this house, and had a fabulous time! The house is beautiful, and set right between two lovely beaches. The house is not...
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From
$139
Per Night
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1 / 8
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Studio, 1 Bathroom, Sleeps 3
Booking
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. Complimentary assigned parking on property and laundry... View all property information
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From
$165
Per Night
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1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Grill
  • Parking
  • Washer
  • Patio
  • Dryer
  • Refrigerator
  • Hot Tub
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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5 of 5 stars Reviewed November 9, 2014
My husband and I stayed at Lanikai Love for 10 days for our honeymoon. We absolutely loved every second of our stay here! The property is exactly as described and even more...
3 of 5 stars Reviewed September 20, 2014
Not pravite pool and hot tub, shared with others lived in that house. No late check out option 11:00 too early. Living room got only fan it's kind hot dining there.
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From
$130
Per Night
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1 / 18
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Hot Tub
  • TV
  • Washer
  • Patio
  • Dryer
  • Stove
  • Parking
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning studio. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$150
Per Night
View Details
1 / 21
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Stove
  • Ceiling Fans
  • Microwave
  • Hot Tub
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$1,350
Per Night
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1 / 19
6 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Washer
  • Patio
  • Stereo System
  • DVD Player
  • Dishwasher
  • Fax
  • Sauna
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
***As of August, 2014, the Kailua Beachfront Retreat will require at least 10 night stays year round.*** With over 3,000 square feet of living space, this 6 bedroom, 5 bath, Kailua Luxury Beachfront Retreat is the perfect place for friends and family to gather and enjoy an amazing experience... View all property information
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From
$425
Per Night
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1 / 42
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • TV
  • Dryer
  • DVD Player
  • Parking
  • Patio
  • Dishwasher
  • Stove
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaiian Style Home, Pool, Tropical Setting, 4 Bdrm, 2 Bath, Short Walk To The Beach, Sparkeling Pool, Lush Tropical Yard Hale Pulelehua “The Butterfly House' has a spacious open feeling inside and out. The large windows front and back allow the trade winds to carry the sweet scent of Hawaiian... View all property information
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From
$225
Per Night
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1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Nearest Beach: 0.0...
  • Number Of Bedrooms
  • HNL: 19.9 mi
  • Living Room Seats...
  • Dining Seats (8)
  • Air Conditioning
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beautiful Single Family Home is sought after neighborhood in Kailua. 15 minutes walk to the beach, Fully furnished with dishes, linens, kitchenware - everything you need. Accommodates 4-6 Some standout features are -- -- 2270 sq feet of house plus a yard that is about 1800 sq feet. -- beautiful... View all property information
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From
$175
Per Night
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1 / 19
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Studio, 1 Bathroom, Sleeps 4
Details Reviews (36) Make Inquiry
Amenities & Details
  • Deck
  • DVD Player
  • Washer
  • Mountain Views
  • Air Conditioning
  • Wi-Fi
  • Refrigerator
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Kailua Bay & Mountain Views! Only 100 yards to Kailua Beach Park! This property is located in Kailua, on Windward Oahu. Relax and unwind in this spacious 3rd floor 1000 sq ft studio. Enjoy your morning coffee on the lanai while listening to the breeze, ocean and rambunctious birds. Watch the... View all property information
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5 of 5 stars Reviewed November 1, 2014
best location in o'ahu….. we had a wonderful stay here, we had everything we needed for a perfect vacation. owners were helpful. the place itself is beautiful and spacious…enjoyed...
5 of 5 stars Reviewed June 2, 2014
Just left this morning and hated to leave. The place looks just like the photos. It was very clean and spacious. The outdoor lanai was very nice and spacious as well. The...
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From
$165
Per Night
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1 / 30
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Parking
  • Grill
  • TV
  • Stereo System
  • Dryer
  • Stove
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully... View all property information
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5 of 5 stars Reviewed November 24, 2014
I highly recomend staying at one of Nancy's cottages in Kailua. The cottage I stayed in was immaculate and had every amenity you could wish for. The owners have created a true...
5 of 5 stars Reviewed October 19, 2014
Nancy's Cottage was recommended to us by friends - it was fabulous! My husband, 19yr old daughter and I went to visit our daughter and boyfriend's family. They only lived about...
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From
$600
Per Night
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1 / 19
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Guest Count
  • Internet Access
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
A cozy and sweet home, Ehu Kai blends a beach cottage feel with luxury. Named for the sea sprays that can be felt from this exceptional property, Ehu Kai is a tranquil retreat, perfect for unwinding from mainland stress. Located at the foot of Kailua Beach, you can escape to total bliss. From the... View all property information
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From
$800
Per Night
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1 / 18
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8 Bedrooms, 4 Bathrooms, Sleeps 18
Details Reviews (3) Make Inquiry
Amenities & Details
  • Garage
  • TV
  • Stove
  • Dishwasher
  • Grill
  • Microwave
  • Refrigerator
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The property is located approx. 10 miles from the city of Honolulu . 15 minutes walk to the nearest beach access. East of the island of Oahu . Surrounded by lush green mountains . The house has tranquil and peaceful atmosphere . This house is fully furnished in an authentic island style. The... View all property information
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4 of 5 stars Reviewed February 19, 2014
On our arrival we were met by Sonya (owner) with cup cakes for the boys. She welcomed us and gave us a tour of her house. House was clean, well decorated, and most of all...
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From
$175
Per Night
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1 / 18
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Studio, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Safe
  • Parking
  • Microwave
  • Stove
  • Patio
  • Washer
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. View all property information
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5 of 5 stars Reviewed September 22, 2014
We loved this wonderful spot. It was as described 5 minutes walk to the beach, beautifully presented, immaculately clean. Eveything we needed was there, they have really thought...
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From
$425
Per Night
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1 / 18
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3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • TV
  • DVD Player
  • Safe
  • Washer
  • Refrigerator
  • Grill
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This three bedroom Lanikai home, plus attached, but private entrance to a completely self contained studio with kitchenette and fully enclose courtyard, is just one short block to Lanikai Beach. Bring the family, and let the grandparents, friends be with you but also have the privacy they need! We... View all property information
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From
$850
Per Night
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1 / 17
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3 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The epitome of island living is experienced in Kailua, Oahu. This home is located at the top of a private road, with direct private access to world renowned Kailua Beach. Enjoy the outdoors and relax in your spacious backyard and private swimming pool. Kailua town is just a short bike ride away,... View all property information
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From
$345
Per Night
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1 / 10
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (7) Make Inquiry
Amenities & Details
  • Grill
  • Ceiling Fans
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
You will find Serenity here. This is the beachfront cottage you've been searching for.This delightful cottage is found in the middle of stunning Kailua Beach. Casually lounge in the small but cozy living room and be astounded by breathtaking views of the beach. Step out your front door and onto... View all property information
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4 of 5 stars Reviewed August 21, 2013
Our family (children age 11 and 9) stayed here for our summer vacation. The location is about as perfect as you can get. A short walk across the lawn right onto one of the most...
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From
$150
Per Night
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1 / 15
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1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
If you're looking for a perfect spot to call home during your stay in Kailua, you'll love this one bedroom/one bath apartment in walking distance of world-famous Kailua and Lanikai Beaches. This unit, which has just been made available as a monthly vacation rental, is tucked away in a quiet,... View all property information
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From
$179
Per Night
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1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Washer
  • Stove
  • DVD Player
  • Safe
  • Ceiling Fans
  • Satellite TV
  • Microwave
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-PALI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the world... View all property information
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5 of 5 stars Reviewed December 18, 2014
This is a rental apartment with the owners living on property. It is nestled into the quiet, private, safe and non-tourist town of Kailua on the western shore. Sure beats paying...
5 of 5 stars Reviewed August 28, 2014
We enjoyed our time in Kailua. The apartment was perfect. We had a lot of space and everything was very clean.
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From
$179
Per Night
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1 / 22
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Pool
  • Dishwasher
  • Patio
  • Grill
  • Safe
  • Stove
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-MAKAI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the... View all property information
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5 of 5 stars Reviewed September 21, 2014
We were a bit apprehensive about being the first renters of this new rental, but took a chance since the location and space seemed ideal. We had a wonderful week staying here...
5 of 5 stars Reviewed November 3, 2014
Apparetement avec piscine très propre et spacieux, accueil sympathique. Je n'hésiterai pas à y retourner.
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From
$450
Per Night
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1 / 10
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Washer
  • Dryer
  • Refrigerator
  • Satellite TV
  • Grill
  • Stove
  • Hot Tub
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It is an easy drive to Sea Life... View all property information
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From
$6,000
Per Night
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1 / 24
7 Bedrooms, 8 Bathrooms, Sleeps 14
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Amenities & Details
  • Fireplace
  • Grill
  • Terrace
  • DVD Player
  • Internet Access
  • Hot Tub
  • Air Conditioning
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Royal Kailua Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green lawn,... View all property information
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From
$995
Per Night
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1 / 25
Payment Protection
6 Bedrooms, 4 Bathrooms, Sleeps 20
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Welcome to Paradise in beautiful Kailua, Hawaii! Our beach villa is about 6000 sqft, is the perfect retreat for everyone. From fresh flowers and sand chairs, kayak, to a blender for tropical drinks, come and have an unforgettable vacation. Take long walks in the morning and enjoy the... View all property information
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$525
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
E Komo Mai! (welcome) Your memorable stay starts as you drive down your private lane into the serenity of a tropical outdoor paradise, providing you with the ultimate island vacation location. Staying true to its Hawaiian charm the 3 bedroom 2 bathroom main home and 1 bed 1 bath separate cottage... View all property information
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$180
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • TV
  • Parking
  • Ceiling Fans
  • Refrigerator
  • Grill
  • Microwave
  • Satellite TV
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Spacious private studio, just 100 yards to lovely Lanikai Beach. Newly renovated interior with Balinese teak and bamboo furnishings, secluded tropical garden with outdoor dining area. The studio is furnished with wood flooring, two comfortable arm chairs, teak furnishings and is adorned with works... View all property information
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$200
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Studio, 1 Bathroom, Sleeps 3
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  • Dryer
  • Refrigerator
  • DVD Player
  • Microwave
  • Stereo System
  • TV
  • Safe
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
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$1,200
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5 Bedrooms, 6 Bathrooms, Sleeps 14
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Amenities & Details
  • Ceiling Fans
  • Refrigerator
  • Microwave
  • Grill
  • Dishwasher
  • Satellite TV
  • Air Conditioning
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Casual accommodations located on Kailua Beach, voted 'Best Beach in the United States' by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu visit. Large outdoor deck spaces provide the perfect place to relax in the sun or enjoy a... View all property information
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$350
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Patio
  • Satellite TV
  • DVD Player
  • Air Conditioning
  • Stove
  • Dryer
  • TV
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Beautiful 2 bedroom & 2 bathroom guest house, with private entrance, in a tropical and quiet setting. Lovely saltwater swimming pool with waterfall and relaxing surroundings. Private barbecue area, with gazebo for outdoor dining, also a luxury kitchen inside. Within walking distance to white... View all property information
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$250
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1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • TV
  • Grill
  • VCR
  • Dryer
  • Patio
  • Refrigerator
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained one-bedroom cottage... View all property information
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From
$165
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Studio, 1 Bathroom, Sleeps 3
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  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our newly renovated studio is the perfect get-away located in the heart of Kailua. Light-filled and breezy this is the perfect space for one or a couple, just minutes away from the beach by foot or bike. Kailua Seahorse Studio is PERFECT. It's even more beautiful in person than in the pictures.... View all property information
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$195
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1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Deck
  • Grill
  • TV
  • DVD Player
  • Refrigerator
  • Dryer
  • Washer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice... View all property information
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$1,200
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6 Bedrooms, 3 Bathrooms, Sleeps 4
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Amenities & Details
  • DVD Player
  • TV
  • Washer
  • Stove
  • Refrigerator
  • Garage
  • Grill
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
One-of-a-kind 5/6 bedroom beachside home on an exclusive street in Kailua. Perfect for a large family with kids or two families to share. Single level architect-designed home was completely rebuilt and renovated in 2007 with the highest quality tropical hardwoods and imported stone. Interiors by... View all property information
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$330
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Parking
  • Air Conditioning
  • Stove
  • Washer
  • Grill
  • TV
  • Microwave
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Makana's Place is a three bedroom, two bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is equivalent to a 4-5 bedroom home. Beautifully decorated with well quality furniture (Koa). Makana's Place features a full kitchen plus... View all property information
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$475
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Stove
  • Microwave
  • Parking
  • Patio
  • Washer
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is... View all property information
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$395
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Microwave
  • Dryer
  • Stove
  • TV
  • Grill
  • DVD Player
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hale Maluhia (House of Serenity) is a kama'aiana style home near Kailua Beach. In a quiet Kailua neighborhood, the home is a quick 5 minute, one block walk to the world famous secluded white sand beach. Relax with friends and family in this child-friendly family home. Experience the warm 'old... View all property information
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$550
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Washer
  • Refrigerator
  • Stove
  • Garage
  • TV
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Endless Summer Getaway.... the name says it all. This fabulous upgraded three bedroom three bath home boasts pride of ownership along with a feeling of hospitality. As you enter into the home you walk into the living/family room, then straight ahead is the sliding door that leads to the outdoor... View all property information
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$300
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Ceiling Fans
  • Stove
  • Washer
  • DVD Player
  • Grill
  • Parking
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a two bedroom rental unit... View all property information
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4 of 5 stars Reviewed October 20, 2014
This is a well appointed, spacious apartment, very close to the beach. Plenty of space for four adults and one small child. Only real negative, is, apart from a small balcony...
5 of 5 stars Reviewed March 10, 2014
I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
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$650
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6 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Garage
  • Microwave
  • Dishwasher
  • Washer
  • Dryer
  • Ceiling Fans
  • Parking
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesnt end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for... View all property information
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$935
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Parking
  • Washer
  • TV
  • Stove
  • Grill
  • Patio
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine... View all property information
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$450
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Stove
  • TV
  • Fireplace
  • Parking
  • Grill
  • Washer
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaiian Paradise, across the street is a short path to Kailua Beach, voted #1 beach in America by Conde Nast Traveler Magazine. A beautiful rather secluded beach far less crowed than most beaches in Hawaii. This private home is a home away from home. This 3 bedroom, 3 Bath property is completely... View all property information
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$900
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5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Grill
  • Refrigerator
  • Microwave
  • Hot Tub
  • Parking
  • Safe
  • TV
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
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$5,600
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2 Bedrooms, 3 Bathrooms, Sleeps 4
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  • Internet Access
  • Ceiling Fans
  • Parking
  • TV
  • Refrigerator
  • Dryer
  • Microwave
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This two bedroom, master-crafted luxury home is located on a quiet lane just steps from world renown Kailua Beach - voted one of the world's best beaches in numerous surveys. The home's island-inspired architecture provides a wonderful sense of place among the tropical vegetation and resort-like... View all property information
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Suitability

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Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.